JPS6322547A - スチルベン類およびその用途 - Google Patents
スチルベン類およびその用途Info
- Publication number
- JPS6322547A JPS6322547A JP62150356A JP15035687A JPS6322547A JP S6322547 A JPS6322547 A JP S6322547A JP 62150356 A JP62150356 A JP 62150356A JP 15035687 A JP15035687 A JP 15035687A JP S6322547 A JPS6322547 A JP S6322547A
- Authority
- JP
- Japan
- Prior art keywords
- methoxy
- phenylethenyl
- carbon atoms
- ethyl
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 235000021286 stilbenes Nutrition 0.000 title claims abstract description 23
- 150000001629 stilbenes Chemical class 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 206010020772 Hypertension Diseases 0.000 claims abstract description 8
- 206010002383 Angina Pectoris Diseases 0.000 claims abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- -1 monoalkylamino Chemical group 0.000 claims description 56
- 125000004432 carbon atom Chemical group C* 0.000 claims description 50
- 150000001875 compounds Chemical class 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 43
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 20
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 125000004414 alkyl thio group Chemical group 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 13
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 9
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 239000001530 fumaric acid Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims description 7
- 125000004423 acyloxy group Chemical group 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 150000003857 carboxamides Chemical class 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 6
- LYUQWQRTDLVQGA-UHFFFAOYSA-N 3-phenylpropylamine Chemical compound NCCCC1=CC=CC=C1 LYUQWQRTDLVQGA-UHFFFAOYSA-N 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 229930192474 thiophene Natural products 0.000 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 3
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 claims description 3
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
- RFGOJWNLUGKNQX-UHFFFAOYSA-N n-[3-(3,4-dimethoxyphenyl)propyl]-1-[5-methoxy-2-(2-phenylethenyl)phenyl]propan-2-amine Chemical compound C=1C=C(OC)C(OC)=CC=1CCCNC(C)CC1=CC(OC)=CC=C1C=CC1=CC=CC=C1 RFGOJWNLUGKNQX-UHFFFAOYSA-N 0.000 claims description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 229940071870 hydroiodic acid Drugs 0.000 claims description 2
- 239000004310 lactic acid Substances 0.000 claims description 2
- 235000014655 lactic acid Nutrition 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 2
- VYIIOQYZUAILCW-UHFFFAOYSA-N n-[2-(2,6-dichlorophenyl)ethyl]-1-[5-methoxy-2-(2-phenylethenyl)phenyl]propan-2-amine Chemical compound ClC=1C=CC=C(Cl)C=1CCNC(C)CC1=CC(OC)=CC=C1C=CC1=CC=CC=C1 VYIIOQYZUAILCW-UHFFFAOYSA-N 0.000 claims description 2
- ZZERSIDGSVWTCG-WYMLVPIESA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-3-[5-methoxy-2-[(e)-2-phenylethenyl]phenyl]-n-methylpropan-1-amine Chemical compound C=1C=C(OC)C(OC)=CC=1CCN(C)CCCC1=CC(OC)=CC=C1\C=C\C1=CC=CC=C1 ZZERSIDGSVWTCG-WYMLVPIESA-N 0.000 claims description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
- 150000003852 triazoles Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 5
- FOBFYHLSTTWDFE-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-1-[5-methoxy-2-(2-phenylethenyl)phenyl]propan-2-amine Chemical compound C=1C=C(OC)C(OC)=CC=1CCNC(C)CC1=CC(OC)=CC=C1C=CC1=CC=CC=C1 FOBFYHLSTTWDFE-UHFFFAOYSA-N 0.000 claims 3
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- DKCXDMOLAKYVDR-UHFFFAOYSA-N n-[2-(3,4-dichlorophenyl)ethyl]-1-[5-methoxy-2-(2-phenylethenyl)phenyl]propan-2-amine Chemical compound C=1C=C(Cl)C(Cl)=CC=1CCNC(C)CC1=CC(OC)=CC=C1C=CC1=CC=CC=C1 DKCXDMOLAKYVDR-UHFFFAOYSA-N 0.000 claims 2
- FOBFYHLSTTWDFE-ZRDIBKRKSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-1-[5-methoxy-2-[(e)-2-phenylethenyl]phenyl]propan-2-amine Chemical compound C=1C=C(OC)C(OC)=CC=1CCNC(C)CC1=CC(OC)=CC=C1\C=C\C1=CC=CC=C1 FOBFYHLSTTWDFE-ZRDIBKRKSA-N 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical group N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 claims 1
- 150000008051 alkyl sulfates Chemical class 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- VYIIOQYZUAILCW-QXMHVHEDSA-N n-[2-(2,6-dichlorophenyl)ethyl]-1-[5-methoxy-2-[(z)-2-phenylethenyl]phenyl]propan-2-amine Chemical compound ClC=1C=CC=C(Cl)C=1CCNC(C)CC1=CC(OC)=CC=C1\C=C/C1=CC=CC=C1 VYIIOQYZUAILCW-QXMHVHEDSA-N 0.000 claims 1
- FOBFYHLSTTWDFE-BENRWUELSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-1-[5-methoxy-2-[(z)-2-phenylethenyl]phenyl]propan-2-amine Chemical compound C=1C=C(OC)C(OC)=CC=1CCNC(C)CC1=CC(OC)=CC=C1\C=C/C1=CC=CC=C1 FOBFYHLSTTWDFE-BENRWUELSA-N 0.000 claims 1
- ZZERSIDGSVWTCG-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-3-[5-methoxy-2-(2-phenylethenyl)phenyl]-n-methylpropan-1-amine Chemical compound C=1C=C(OC)C(OC)=CC=1CCN(C)CCCC1=CC(OC)=CC=C1C=CC1=CC=CC=C1 ZZERSIDGSVWTCG-UHFFFAOYSA-N 0.000 claims 1
- YFYMJUPQZURXRZ-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-4-[5-methoxy-2-(2-phenylethenyl)phenyl]butan-2-amine Chemical compound C=1C=C(OC)C(OC)=CC=1CCNC(C)CCC1=CC(OC)=CC=C1C=CC1=CC=CC=C1 YFYMJUPQZURXRZ-UHFFFAOYSA-N 0.000 claims 1
- YFYMJUPQZURXRZ-SDNWHVSQSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-4-[5-methoxy-2-[(e)-2-phenylethenyl]phenyl]butan-2-amine Chemical compound C=1C=C(OC)C(OC)=CC=1CCNC(C)CCC1=CC(OC)=CC=C1\C=C\C1=CC=CC=C1 YFYMJUPQZURXRZ-SDNWHVSQSA-N 0.000 claims 1
- SDFGNBUWEIUESZ-UHFFFAOYSA-N n-[2-(3,5-dimethoxyphenyl)ethyl]-1-[5-methoxy-2-(2-phenylethenyl)phenyl]propan-2-amine Chemical compound C=1C(OC)=CC(OC)=CC=1CCNC(C)CC1=CC(OC)=CC=C1C=CC1=CC=CC=C1 SDFGNBUWEIUESZ-UHFFFAOYSA-N 0.000 claims 1
- SDFGNBUWEIUESZ-KHPPLWFESA-N n-[2-(3,5-dimethoxyphenyl)ethyl]-1-[5-methoxy-2-[(z)-2-phenylethenyl]phenyl]propan-2-amine Chemical compound C=1C(OC)=CC(OC)=CC=1CCNC(C)CC1=CC(OC)=CC=C1\C=C/C1=CC=CC=C1 SDFGNBUWEIUESZ-KHPPLWFESA-N 0.000 claims 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 5
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 125000003118 aryl group Chemical group 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract description 2
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 206010003119 arrhythmia Diseases 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 68
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 57
- 239000000243 solution Substances 0.000 description 53
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 239000000203 mixture Substances 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 238000002844 melting Methods 0.000 description 21
- 230000008018 melting Effects 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 239000002904 solvent Substances 0.000 description 19
- 239000003921 oil Substances 0.000 description 18
- 235000019198 oils Nutrition 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- 239000012267 brine Substances 0.000 description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 239000012458 free base Substances 0.000 description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 150000001502 aryl halides Chemical class 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 235000011181 potassium carbonates Nutrition 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- RPZRPEAONLVFLV-UHFFFAOYSA-N 4-(2-iodo-5-methoxyphenyl)butan-2-one Chemical compound COC1=CC=C(I)C(CCC(C)=O)=C1 RPZRPEAONLVFLV-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 150000001336 alkenes Chemical group 0.000 description 4
- 230000004872 arterial blood pressure Effects 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 150000002466 imines Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 239000002808 molecular sieve Substances 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
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- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
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- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- IKESLYZGJVYKLN-UHFFFAOYSA-N n-[2-(2,6-dichlorophenyl)ethyl]-1-(2-iodo-5-methoxyphenyl)propan-2-amine Chemical compound COC1=CC=C(I)C(CC(C)NCCC=2C(=CC=CC=2Cl)Cl)=C1 IKESLYZGJVYKLN-UHFFFAOYSA-N 0.000 description 1
- QHNNBMBPOXANQU-VHPXAQPISA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-1-[5-methoxy-2-[(e)-2-phenylethenyl]phenyl]propan-2-amine;hydrochloride Chemical compound Cl.C=1C=C(OC)C(OC)=CC=1CCNC(C)CC1=CC(OC)=CC=C1\C=C\C1=CC=CC=C1 QHNNBMBPOXANQU-VHPXAQPISA-N 0.000 description 1
- QHNNBMBPOXANQU-BBJSDXRSSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-1-[5-methoxy-2-[(z)-2-phenylethenyl]phenyl]propan-2-amine;hydrochloride Chemical compound Cl.C=1C=C(OC)C(OC)=CC=1CCNC(C)CC1=CC(OC)=CC=C1\C=C/C1=CC=CC=C1 QHNNBMBPOXANQU-BBJSDXRSSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- KNMVKIOORFJHKF-UHFFFAOYSA-N n-benzyl-2-phenylethenamine Chemical class C=1C=CC=CC=1CNC=CC1=CC=CC=C1 KNMVKIOORFJHKF-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012057 packaged powder Substances 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- QJPQVXSHYBGQGM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- DQMFXGQHSPWNOA-UHFFFAOYSA-N triethylazanium;sulfamate Chemical compound NS([O-])(=O)=O.CC[NH+](CC)CC DQMFXGQHSPWNOA-UHFFFAOYSA-N 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/213—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C49/217—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings having unsaturation outside the aromatic rings
- C07C49/223—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings having unsaturation outside the aromatic rings polycyclic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Control And Other Processes For Unpacking Of Materials (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87662886A | 1986-06-20 | 1986-06-20 | |
| US876628 | 1986-06-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6322547A true JPS6322547A (ja) | 1988-01-30 |
Family
ID=25368200
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62150356A Pending JPS6322547A (ja) | 1986-06-20 | 1987-06-18 | スチルベン類およびその用途 |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0250254B1 (da) |
| JP (1) | JPS6322547A (da) |
| AT (1) | ATE64591T1 (da) |
| AU (2) | AU7453487A (da) |
| DE (1) | DE3770878D1 (da) |
| DK (1) | DK315587A (da) |
| ES (1) | ES2025164B3 (da) |
| GR (1) | GR3002168T3 (da) |
| ZA (1) | ZA874448B (da) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4772755A (en) * | 1987-03-19 | 1988-09-20 | Mcneilab, Inc. | 1,2-1,4 addition reaction sequence leading to disubstituted acelylenes |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3719712A (en) * | 1969-09-29 | 1973-03-06 | Merck & Co Inc | 2-phenylethynyl-benzyl-amines |
| SE388603B (sv) * | 1971-01-15 | 1976-10-11 | Merck & Co Inc | Forfarande for framstellning av en fenylalkylaralkylamin med antiarytmisk verkan |
| CA1292747C (en) * | 1983-11-21 | 1991-12-03 | John Robert Carson | Aralykyl (arylethynyl) aralkyl amines and their use as vasodilators and antihypertensives |
-
1987
- 1987-06-18 JP JP62150356A patent/JPS6322547A/ja active Pending
- 1987-06-18 ZA ZA874448A patent/ZA874448B/xx unknown
- 1987-06-19 EP EP87305453A patent/EP0250254B1/en not_active Expired - Lifetime
- 1987-06-19 AU AU74534/87A patent/AU7453487A/en not_active Abandoned
- 1987-06-19 DE DE8787305453T patent/DE3770878D1/de not_active Expired - Fee Related
- 1987-06-19 ES ES87305453T patent/ES2025164B3/es not_active Expired - Lifetime
- 1987-06-19 AT AT87305453T patent/ATE64591T1/de active
- 1987-06-19 DK DK315587A patent/DK315587A/da not_active Application Discontinuation
-
1991
- 1991-05-03 AU AU76375/91A patent/AU7637591A/en not_active Abandoned
- 1991-06-20 GR GR91400842T patent/GR3002168T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU7637591A (en) | 1991-08-08 |
| ZA874448B (en) | 1989-02-22 |
| DK315587A (da) | 1987-12-21 |
| ATE64591T1 (de) | 1991-07-15 |
| EP0250254B1 (en) | 1991-06-19 |
| AU7453487A (en) | 1987-12-24 |
| DE3770878D1 (de) | 1991-07-25 |
| DK315587D0 (da) | 1987-06-19 |
| ES2025164B3 (es) | 1992-03-16 |
| EP0250254A1 (en) | 1987-12-23 |
| GR3002168T3 (en) | 1992-12-30 |
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